Stannane, tributyl(1-ethoxyethenyl)- → 6-acetyl-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 1 g of 3-(3,4-dimethoxybenzyl)-6-iodo-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione, 1.3 ml of tributyl(1-ethoxyvinyl)tin and 0.04 g of Pd(PPh3)4 in 20 ml of toluene is heated for 1 hour at 130° C. and then stirred for 48 hours at room temperature. The solvent is evaporated off under reduced pressure. The residue is taken up in EtOAc and washed four times with 4N HCl and then with water. The organic phase is dried over Na2SO4, filtered and evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/EtOAc mixture from (80/20, v/v) to give 0.84 g of the expected product.

Provenance & Evidence